Kal Penn’s Busy Onscreen Year Includes Playing Anna Nicole Smith’s Doctor, A Gregg Araki Role & ‘Harold & Kumar 4’ In Works: “One Of The Funniest Scripts”

Following years of juggling acting and political work, supporting the likes of President Obama and NYC Mayor Mamdani, Kal Penn is back in leading man mode.

A day after wrapping his role in Gregg Araki‘s The Decline of Fucking Western Civilization, Deadline caught up with the actor about his busy onscreen year that culminates with his portrayal of the late Anna Nicole Smith’s physician, Dr. Sandeep Kapoor, in writer/director Thane Economou’s Trust Me, I’m a Doctor, which is now playing in theaters.

“I was really fascinated mostly with the insecurity of the character of Sandeep, and the vulnerability and this push and pull between—I think five times in the movie, he says, ‘I’m just a private person, living a private life,’ but then makes every decision contrary to that, just to get attention, right?” explained Penn. “So, there was that kind of juiciness to a character that I hadn’t played before that attracted me to it.”

Based on Kapoor’s 2017 memoir Trust Me, I’m A Doctor: My Life Before, During and After Anna Nicole Smith, the Economou-helmed biopic recounts the doctor’s professional relationship with Smith as his patient, which was blurred when they began a brief friendship outside the exam room, before her death of a prescription drug overdose.

Although the Medical Board of California launched a review of Dr. Kapoor for prescribing methadone to Smith under a pseudonym in the eighth month of her pregnancy, he was acquitted on all legal counts in Smith’s death and allowed to continue his medical practice.

Penn found during prep for the Briarcliff film that “the real Sandeep was, to my surprise, very welcoming in letting me shadow him, follow him around.”

“I had dinner with him tons of times, and I think through that, saw a couple of things that made me think. There are things that he does physically. He sits differently based on who he’s with. If it’s somebody he’s clearly nervous in front of, he sits very differently than friends or family he’s comfortable with. His manner of speaking and his flamboyance also, not that he’s code-switching, but they clearly switch based on who he’s around,” he added.

Telling Kapoor’s story of his experience with Anna Nicole also involved a “guerrilla style” scene filmed in the middle of the 2024 West Hollywood Pride Parade, made to look like WeHo in 2005.

“Thane, our director, basically had 30 background artists surrounding this car, and it, shot-for-shot, needed to look like the real parade that Anna and Sandeep went on, so everything else in the background is mostly out of focus, unless you could get away with the few things that are remaining from 20 years ago, like Circus of Books,” Penn noted. “But it was super interesting because you also only had one shot, right? You start at the beginning of the parade and you go through to the end and hope that you get everything you need.”

And while Larry Birkhead, the father of Anna Nicole’s daughter Dannielynn, has expressed his disapproval of the project, Penn concedes that “not gonna be a movie for everybody,” but acknowledges that “somebody tragically died, and I would never want to make light of something like that in a film.”

With a busy year coming to a close, which included a “fun” arc as “a terrible person” in Season 4 of BBC/HBO’s Industry, Penn is getting ready to return to his roots following last year’s news of a fourth Harold & Kumar in the works from writers Jon Hurwitz, Hayden Schlossberg and Josh Heald.

“So, John Cho and I have formally signed on for a fourth film,” confirmed Penn. “Jon and Hayden, the amazing screenwriters who’ve written all three movies, they directed the second one, they will direct the fourth one, and they just finished the script, which John and I both read a couple of weeks ago, and I loved it. It tracks with the other three movies, and I’m not just saying this because I play the guy, but it’s one of the funniest scripts that I’ve read in a very long time.”

Penn added, “So I’m excited, but it hasn’t yet been greenlit or anything, so I don’t have any actual updates, other than that I read the script and loved it. So hopefully, we get to make the thing.”

Meanwhile, Penn has been busy checking off a bucket list item after working with New Queer Cinema director Gregg Araki on his next film, The Decline of Fucking Western Civilization, a role he told his agent to “aggressively pursue” after he first saw Araki speak after a UCLA screening of his 1995 film Doom Generation during Penn’s undergrad years.

“I didn’t know anything about the film, you just kind of walk in. I’m like, ‘This is unlike anything I’d ever seen before.’ And then listening to his Q&A about his kind of guerrilla-style filmmaking and shooting in LA and just doing things the way that he always has done—” recalled Penn. “So, I was thrilled to join the cast, and I just wrapped.”

Read on about Kal Penn’s experience playing Dr. Sandeep Kapoor in Trust Me, I’m a Doctor, now in theaters, as well as his upcoming roles in Harold & Kumar 4, Gregg Araki’s The Decline of Fucking Western Civilization and more.

DEADLINE: What was it about this perspective of Anna Nicole’s story that appealed to you?

KAL PENN: So, I didn’t know very much about her story, and if I’m being honest, I still don’t, because the arc of playing Sandeep in the film is kind of start-to-finish from before he meets Anna to after her passing. And so, I never did the research into her, cause it just made it easier to be Sandeep. And then you wrap a film, and you’re like, “OK, that was it.” … But the reason I said yes to the movie, I remember being a young actor in LA, at the nascent days of reality TV, and I think there was one party I went to, like an awards show, that Anna was at, but she was there with like four cameras and a huge entourage, and it was clear she was shooting a reality show. But I remember my friends and I were like, “Oh, does she have a reality show because that’s how she actually behaves, or is she behaving that way because she has a reality show?” And that’s a question that the film doesn’t fully answer either, it’s an open question by the end of our movie. But that’s all I knew about her, right? It’s like, “Oh yeah, that’s Anna Nicole Smith from that reality show.” So, I see the email come in from my agent for this movie, and it was a short logline that I just skimmed, and then the script was attached. And as I’m clicking on the script, I think to myself like, “Oh yeah, I know this story. This is about that doctor who’s in prison for murdering Anna Nicole Smith.” And then I started reading the script, I was like, “This is not at all what happened. How do I think that’s what happened?” I never followed the case or anything, but why do I think that’s what happened? And then I was like, “Am I one of these people who reads three tweets and thinks I’m an expert on something?” So, I read the script with that in my head and was really fascinated mostly with the insecurity of the character of Sandeep, and the vulnerability and this push and pull between—I think five times in the movie, he says, “I’m just a private person, living a private life,” but then makes every decision contrary to that, just to get attention, right? So, there was that kind of juiciness to a character that I hadn’t played before that attracted me to it.

DEADLINE: What was it like undergoing the physical transformation and changing your voice for the role?

PENN: So obviously, Anna Nicole Smith was in the public eye as a character. Sandeep is an interesting character to play because he wasn’t. I guess he was in the public eye, and therefore fair game and all of that, but he’s not like a household name, and I think the biggest decision in trying to figure out with Thane, our writer-director, about the right way to play him was like, “I just need to ground these vulnerabilities, and these poor ethical decisions in something bigger than what’s on the script,” and the real Sandeep was, to my surprise, very welcoming in letting me shadow him, follow him around. I had dinner with him tons of times, and I think through that, saw a couple of things that made me think. There are things that he does physically. He sits differently based on who he’s with. If it’s somebody he’s clearly nervous in front of, he sits very differently than friends or family he’s comfortable with. His manner of speaking and his flamboyance also, not that he’s code-switching, but they clearly switch based on who he’s around. So, there was a bit of Alexander Technique, there was a bit of backstory to ground all of that, but that’s kind of what went into the transformation. It isn’t necessary because for me, it made a lot of sense, some of the things that you kind of learn about him based on all that.

DEADLINE: It’s funny you bring that up because that was one part of it that I really resonated with, his experience as a closeted gay man, and that one scene at the West Hollywood Pride Parade really made me happy, just seeing that through his eyes, not just befriending Anna Nicole, but being around all of these people who accept him for him, and I’m curious what was it like for you filming that scene?

PENN: That scene is an interesting one, especially hearing your take on it, because in reality, Sandeep told me he had been to the Abbey tons of times with his friends, always had a great time, but generally felt invisible in that space. So, guys weren’t coming up to him to strike up a conversation. Some of that may have been because he’s a nerdy brown doctor, and Weho at that time especially was fairly homogeneous, the standard of beauty was very different. It still is like that, but thankfully less so compared to 20 years ago. So, what he had told me, and this actually ties into an earlier part of getting to know him a little bit, when I shadowed him for the first time, something clicked. I went to his office, it’s still in the Valley, same office as before, it’s small. And when you go in, there are like three receptionists, and his little waiting room, and then maybe three exam rooms. Glenn, I don’t know about you, but when I make an appointment to see my doctor, I either talk to a fucking AI slop bot that makes my blood boil, or I have to log in and pick a slot. And in both cases, there’s no appointments for like seven and a half weeks. So, when I saw the way that Sandeep works, and there’s a human who picks up the phone and he knows all of his patients … it was that 1950s personal touch of doing medicine that immediately made me recognize, “OK, it’s not weird that Anna invited him to Pride,” because it was common for him to get invitations to somebody’s bar mitzvah, or your patient’s Super Bowl party. Those were just things that would happen. So, when Anna invited him to the Pride Parade and then to the Abbey, it made sense that he would go. What didn’t make sense is, you could have two champagnes with your patient/acquaintance. Don’t have nine bottles of champagne with her, and then don’t make out with her on the couch next to the dance floor. These are objectively horrendous decisions, right? So, I think knowing all of that and then knowing in the real world, this was very grounding for me, knowing that the real Sandeep had been to the Abbey and enjoyed it, but the way he was experiencing it through the lens of Anna, it was clear to him that he was getting tons of attention from all of these people, because he was in her proximity and her orbit, and he knew that wasn’t real for him. But it was so intoxicating for the night, that to me that was fun, it was tragic, it was heartbreaking. It was also no sympathy for somebody who’s making bad decisions. It was all of those things, it was a night at the Abbey, you know?

DEADLINE: Yeah. Did y’all actually shoot at the Abbey?

PENN: No, we shot most of the movie in Toronto, so this was a nondescript club in Toronto. The only stuff we shot in the states, in LA, was the Pride Parade stuff.

DEADLINE: Yeah, I was gonna say I saw y’all going past Circus of Books. Was it actually filmed during the Pride Parade?

PENN: Yeah, it was guerrilla style, so Thane, our director, basically had 30 background artists surrounding this car, and it, shot-for-shot, needed to look like the real parade that Anna and Sandeep went on, so everything else in the background is mostly out of focus, unless you could get away with the few things that are remaining from 20 years ago, like Circus of Books, so that’s why you got a good shot of that. but it was super interesting because you also only had one shot, right? You start at the beginning of the parade and you go through to the end and hope that you get everything you need.

DEADLINE: What was it like shooting the make-out/vomit scene, cause that seems like it could have gone wrong.

PENN: It was fun. I mean, it was one of those scenes that it’s like 7:30 in the morning in a dingy club in Toronto. I know the story that everybody wants to hear is, “Was it late at night and were you guys having a good time?” Yes, we were having a good time. It’s just like, first up after brushing your teeth, you get to puke.

DEADLINE: It broke my heart that he was forced to publicly come out in order to save his career, but it did make me happy when he finally came out to his dad. Tell me about exploring that dynamic.

PENN: It’s funny, a lot of people are asking about that dynamic. I think it’s interesting because it’s not as compelling to me as the horrific decisions that he made. I know why we have it in the script, because you need something personal to flavor this. Otherwise, it’s a legal drama, but the parts that drove the stuff that maybe culminates with the scene with his dad, there are multiple scenes that I have with Linda Hamilton, where I, as Sandeep, am withholding critical legal information from my defense lawyer, which is like, “Why would you do that?” And it shows you the psychology of, he thinks that he’s doing the right thing. So no matter what missteps he’s making, and I think now having it out there and audiences seeing it, watching it, going, “Do not make this decision, I’m watching a train wreck, I’m passing a car accident on the 405, I know it’s gonna be bad. I know you’re making this decision. I wish you wouldn’t—yep, there you go, you did it.” It’s like, understanding why he does that, he thinks it’s gonna be the right thing. I remember asking him, “Why did you take the files home from your office?” And hindsight… Sandeep’s like, “It’s two things. One, I probably shouldn’t have, clearly.” But he had paparazzi posing as patients, coming into his office, trying to get appointments with him. And he genuinely believed that they were gonna come in, break in in the middle of the night, and steal Anna’s files, and all of her medical information would get out there. And I was just like, “Yeah, but the only other choice was to take home the files?” I’m like, “Bro, this does not add up. Those are not the only two choices in life, right?” So to me, it’s the way that he talks himself into this circle of poor decision-making that I never considered were for him, a lie on a lie on a lie. And I think in exploring the relationship with his dad, you can see the weight that had on him. In real life, if I’m remembering this correctly, the real Sandeep was very open with his mom and with all of his friends, and so, crafting that relationship with the dad and the parents was, I think for Thane, a little bit more of a creative liberty for the film. It’s also why I think I gravitate so much towards the bad decisions that he made with his vulnerability as opposed to any of the identity stuff, whether it’s ethnic identity or sexuality or anything like that.

DEADLINE: I’m curious if you’ve, happen to have seen Larry Birkhead’s response?

PENN: I did, yeah.

DEADLINE: What were your thoughts?

PENN: You know, I didn’t really have thoughts on it, only because I think I was so hyper-focused on trying to bring Sandeep to life. I also know very little about the real Anna Nicole Smith. I think the one thing that that was important to me was, somebody tragically died, and I would never want to make light of something like that in a film. So, I remember asking Thane, I was like, “This is kind of being pitched as a dark comedy. I hope the comedy is not in the tragic passing of this woman.” He’s like, “No, no, no, of course not.” And then you read the script and you see the dark comedy comes from the self-deprecation of Sandeep. But of course, I mean, people will have their opinions on it. It’s not gonna be a movie for everybody, and so if there are folks who feel like this is disturbing for any reason, I’m not the guy who’s like, “You should see it anyway.” You should skip this one.

DEADLINE: I know that someone was talking about a fourth Harold and Kumar not too long ago. Is that happening?

PENN: Yeah. … So, John Cho and I have formally signed on for a fourth film, which I think Deadline reported on a couple of months ago. Jon [Hurwitz] and Hayden [Schlossberg], the amazing screenwriters who’ve written all three movies, they directed the second one, they will direct the fourth one, and they just finished the script, which John and I both read a couple of weeks ago, and I loved it. It tracks with the other three movies, and I’m not just saying this because I play the guy, but it’s one of the funniest scripts that I’ve read in a very long time. … You kind of can’t make a movie like this unless it sticks with the satire and the reflection of what’s happening in the world, in a way that only I think Jon Hurwitz and Hayden Schlossberg can write, and I just thought it was so smartly done with the appropriate amount of the dumb jokes that always come with the Harold & Kumar movie, so I’m excited, but it hasn’t yet been greenlit or anything, so I don’t have any actual updates, other than that I read the script and loved it. So hopefully, we get to make the thing. I usually text them once every two and a half, three weeks to be like, “Any updates?” So, I will do that this afternoon.

DEADLINE: I love the franchise, and I’m curious, are you and John Cho down to keep this franchise going to the grave? We see Cheech and Chong still out there, kicking it.

PENN: You’d have to ask John for his thoughts. I can tell you that over the years, I think after the starting with the second movie, I was basically like, “My gosh, what good fortune do I have to be able to make these kinds of things?” I had loved comedy before, obviously not to compare Harold & Kumar to something that I revere, but one of the things I loved about the writing from the Jon and Hayden brains was that it almost reminded me of … one of the reasons that I loved the Muppets, and never shed my love for the Muppets in the years since, is that some of the early Muppet movies, there are jokes that are clearly in there for the adults in the room, and then there’s the other stuff for the kids. And I think that what they do with these movies is, if you just wanna walk in and laugh with your friends, which is really the goal ultimately, satire and commentary aside, the number one goal of these things is always to just make anybody laugh. You laugh and you leave happy with your friends, and if you wanna find the satire in it and you like that, that’s obviously in there for you too. So, I just sort of loved that and was like, “I feel lucky to begin with that we made, we got to make three of them. I’d be very happy if we made 50 of them before I died.” I just think that the character is also so much cooler than I will ever be, and especially as the world has gotten more and more polarized, it’s one of the things I love about those characters is that it means a lot to me. I’ve talked to Jon and Hayden about this, and they feel the same way. It means a lot to us that people enjoy it across the political spectrum, and that’s been very cool, that in a world in which we have relatively few things that we can do together anymore, I like that food, comedy, movies, music, those are still things that can kind of have that magic, and that’s been very cool to see also.

DEADLINE: Well, as a gay stoner who went to Harold & Kumar in theaters when I was in middle school, I’m looking forward to the next one.

PENN: Oh, thank you. OK, you’re a gay stoner—I just wrapped this Gregg Araki movie yesterday.

DEADLINE: I love Gregg. You’re working with him on The Decline of Fucking Western Civilization? Awesome title. How did you come onto the project?

PENN: So, I signed with Anonymous Content recently, and my manager basically reached out. It was like, “There’s a role in the new Gregg Araki movie—” and I like interrupted it, but I was like, “OK, let’s go ahead and make that happen.” He’s like, “Well, I’m sending you the script, and here’s all the details for the meetings and the all of that.” It was one of those things, it almost sounds cliche, but I was like, “I mean, obviously I will read it, but I can tell you right now I would like to aggressively pursue this.” And part of the reason was, the first movie I saw when I moved out to LA, I did undergrad at UCLA, and it was literally the first week of theater and film school. There was a Doom Generation screening on campus, and Gregg and the cast came to do a panel and a Q&A. And I didn’t know anything about the film, you just kind of walk in. I’m like, “This is unlike anything I’d ever seen before.” And then listening to his Q&A about his kind of guerrilla style filmmaking and shooting in LA and just doing things the way that he always has done—which when I talked to him about this movie, I obviously told him that story. But he’s like, “You know, I always shoot in LA. I’ve never shot anywhere else.” And he’s just sort of walking you through the things that I guess I knew as a Gregg Araki fan, but it was very cool to actually hear. So, I was thrilled to join the cast, and I just wrapped.

DEADLINE: You’ve been doing a lot of really cool roles lately, and I was also curious about joining Industry for Season 4. What was it like working with those guys?

PENN: That was awesome. Mickey [Down] and Konrad [Kay] are two of the smartest and most insane writers. Every script that we had, I was like, “This is amazing. I can’t believe I get to do and say this.” I don’t know what most actors say, but I’ll tell you, I always feel like, playing a terrible person is way more fun than than playing somebody who’s good. And so, the Industry world, I was a fan of before, because it’s a world that I don’t actually know personally, but the scripts and the storylines were so insane that that was another one where that kind of offer came through, and I was super excited. It turned out that both of them are actually big Harold & Kumar fans, which is how I guess my name entered their psyche for this particular role. And I loved that they kind of counter-cast it, like Kumar is this wonderfully gregarious, friendly guy who’s everybody’s best friend, and the Jonah character I play in Industry is very much the opposite, incredibly flawed, womanizing, misogynistic, greed-fueled, at least you think so until you realize he also got fucked over by Max Minghella’s character. But I had the best time making that. We were in London and Cardiff for I guess about two months last year, and those are the kind of writers where they’re so smart—to me, that show is not binge-able because it’s so dark, in the same way that Succession was not binge-able for me, which is a testament to how good it is, where it’s like I need a week or two between episodes to sit with this. I need to sit with it and think about it. But then, the rewatch rate for me is super high also, where I’ll go back and catch things that I hadn’t caught the first time. Just kind of placing a lot of those things in the work when you’re doing that was great. And most of my scenes were with Max Minghella, who I just think the world of. What a phenomenal actor and director.

DEADLINE: But I know your character Jonah might have an ax to grind. Do you think he could potentially come back for Season 5?

PENN: I would love if he did. I don’t know if he will. Look, I’ll take him if he comes back. I definitely think he left with a huge ax to grind, and the last scene that you see him in is just wasted at a strip club in Miami, so who knows where he goes? But you know what, let me pitch him, to throw this one out there. He he could do a spin-off. That’d be fine… I mean, that’s not a real thing.

DEADLINE: Let’s just manifest it.

PENN: Sure, sure, I’d do that. My point is, it’s rare to have kind of all those layers and that darkness to a world. Prepping for that, I remember texting either Mickey or Konrad. I was like, “Hey, I’m walking around. I had a list of places where bankers go in London, Canary Wharf. What’s a good bar if I wanna just listen and eavesdrop on conversations with bankers?” And they’re like, “Why would you do that? Go have a nice fucking meal at Chiltern Firehouse. Don’t.” I was like, “No, no, no, guys. Come on, I’m not method, but I’ve got this week to immerse myself in this insanity.” I just think they’re so thoughtful, they know that world really well, but they’re not restricted by it. The friends I talked to who work in that world, they’re like, “Yeah, a lot of that stuff comes from a very real place.” It’s clear that they had spent time there before crafting these characters, and so, as somebody with very little business sense, I just love a good nerdy deep dive into character background and what the hell I’m actually doing, learning all the terms. … I love the research that goes into it. And so, for something like Industry, even for a half-season arc, it was cool to just be fully immersive and kind of learn as much about that world as possible, to bring that shady dude to life.

DEADLINE: I know you have a few other upcoming projects. Can you say anything about Contra or What the Fuck Is My Password?

PENN: Yeah, What the Fuck Is My Password is very funny. It’s basically abou, a guy who essentially loses a crypto password, and things that happen to him after that. I’ll be vague because I can’t remember how much they put out there, but it was very funny. We shot that in New Jersey. And then Contra is this super dark, almost like a 1980s style chess thriller that’s based on—I didn’t know that this was real. There are these underground chess competitions called Contra, where basically these really good world-class chess players will get a shady sponsor who has to drop like $100,000 as an entry fee, for example, to these underground competitions, in the hopes that they also will then recoup most of the winnings, go to the person who invested in the entry fee for this contestant. So, this is a movie about the underworld of that and the greed. So, I play a not nice guy. I play one of the gangsters who’s kind of controlling one of these Contra chess organizations. It was very cool. We shot in Bangkok last year, and I think they’re wrapping up post now. But it was interesting, the movie doesn’t take place in Bangkok, so it was one of those tax benefit things that I guess the producers felt like that was the best place to shoot. But the crews are fantastic. It’s definitely a grittier feel. I haven’t seen the rough cut yet, but at least what they were going for stylistically was the Rambo, Terminator, late 1980s, early 1990s kind of feel. So visually, I think it’ll look pretty wild.